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3. Give the structure of the product expected 7. Biphenyl (phenylbenzene) undergoes the
from the reaction of each of the following com- Friedel-Crafts acylation reaction, as shown by
pounds with benzene in the presence of one the follwoing example.
equivalent of AlCl3, followed by treatment with
water. + Cl – C – CH 3
1)AlCl3
C – CH3 + HCl
2)H2O
biphenyl
(A) (CH3)2CH – C – Cl
p-phenylacetophenone
On the basis of this result, what is the direct-
ing effect of the phenyl group ?
(B) C – Cl
8. Predict the predominant products that would
lsobutyryl chloride result from bromination of each of the follow-
ing compounds. Classify each substituent group
benzoyl chloride as an ortho, para director or a meta director.
and explain your reasoning
4. Show two different Friedel-Crafts acylation
reactions that can be used to prepare the ..
following compound. (A) NH – C – CH3
CH3
(B) CF3
C CH 3
+
(C) N(CH3)3
CH3
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9. Explain why the nitration of anisole is much 14. When the following compound is treated with
faster than the nitration of thioanisole under H2SO4 the product of the resulting reaction
the same conditions. has the formula C15H20 and does decolorize Br2
.. in CCl4. Suggest a structure for this product
OCH3
.. and give a curved - arrow mechanism for its
formation.
..
SCH
.. 3
OH
CH3
anisole thioanisole
H2SO 4
?
10. Which should be faster bromination of ben-
zene or bromination of N,N - dimethylaniline?
Explain your answer carefully.
15. Write the principal organic product in each of
the following reactions:
..
N (CH3)2 Cl
NO2
N,N - dimethylaniline
CH3
Cl
C – CH3
NO2
(ii) H
2 NNH 2
B
NO2 triethylen e
glycol
NO2
12. Give the products expected(if any) when
ethylbenzene reacts under the following con-
ditions.
(A) Br2 in CCl4 (dark)
CF3
(B) HNO3 ,H2SO4
(C) conc. H2SO4
(D) C2H5 – C – Cl,AlCl3(1.1 equiv.) then H2O (iii) ( i ) HNO 3 , H 2SO 4
C
( ii ) NaOCH , CH OH
3 3
(E) CH3Br,AlCl3
(F) Br2,FeBr3 Cl
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Page # 30 AROMATIC COMPOUNDSE
dichloride
isomers with formula C15H12O2)
(v) Br OCH3
(D) + HNO3 H
2SO 4
0 C
CH3
(i) NBS,Benzoylperoxide,CCl4 .heat
E
(ii) NaSCH 3
Cl
(E) ferrocene + H 3C – C – Cl 1
) AlCl 3
2 ) H 2O
NO2 (C12H12OFe)
NO2 OH
Cl Br2
17. Product A and B is
H 2O
NO2
(vii) + C6H5CH2SNa G
Br2
B
NO2 CS2
Product A and B is
O – CH 2CH 2CH – Cl
(B) AlCl
3 Exercise-IV (Matrix)
CH 3
1. Substituent on phenyl ring.
(a compound with ten carbons)
(A) – CH2 – CH3
(P) o/p - directors
Cl – C – C – C – Cl
(C) +
(B) – O – S – CH3 (Q) meta directors
H3 C CH3
1
) AlCl 3
(three products, all
2 ) H 2O (C) – NH – C – CH3 (R) Activating group
naphthalene
-dimethylmalonyl (D) – S – CH3 (S) Deactivating group
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2. Column I
(A) CO2 is evolved from O – CH = CH2
(B) Libbermann nitroso test is given by
(C) Compounds gives yellow oily
(P)
(D) (S) meta- director
(R) R – NH – R
liquid on reaction with NaNO2 + HCl
CH3
S –Et
5. Match th column :
X OCH3
NO2 NO2
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Page # 32 AROMATIC COMPOUNDSE
X = halogen
relative reactivity toward (SNAr) OH
(A)– F (P) 312
(B) – Cl (Q) 1
6. Matrix : Reaction
Product Ph OH
(S) C=N PCl
5
CH3
F
carbon increases
CHO
Cl (A)
(B) CHFCIBr
KOH , + –
NH 2 NC
(B)
Br
(C) CHCI
2 Br
KOH ,
NH 2
(C) Ph—NH2
(D) CHBr
2 CI
KOH ,
N – OH
7. Column-I
(A) Caprolactum formation take place in
(D) Ph – C – Ph Ph – C – NH – Ph
(B) Beckmann rearrangement is
(C) Schmidt reaction is
(D) Reaction in which number of Column-II
Column-II (P) CHCl3 / KOH
(Q) Br2 / KOH
(R) H2SO4
(S) PCl5
(P) HN
3 9. Matrix
H 2SO 4 Column-I
N – OH (A) HNO
3
H 2SO 4
H
(Q)
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AROMATIC COMPOUNDS Page # 33
OH
Br2 (A)
(C)
H 2O
CH3 Br
Br2 OH OH
(D)
Fe
Br Br
Column - ll
(P) Carbocation is intermediate (B)
(Q) Carabanion is intermediate
(R) Electrophilic substitution reaction CH3 Br
(S) Rearrangement takes place
10. Column-I
OH OH
Br
(A) + CO + HCl AlCl
3 (C)
(B) Ph – C = N SnCl
2 / HCl
H 2O
NH2 NH2
CH3
CrO 2 Cl2
(C)
H 2O
(D)
CH3 Br
(D) Ph – C N H 3O
Column-II 12. Which of following is the incorrect major prod-
(P) Ph – CHO is product uct ?
(Q) Etard reaction
(R) Stephon reduction OCH3 OCH3 CH3
(S) Gattermann Koch reaction
(T) Ph – CO2H
CH3
Comprehension - 3 (11 to 13) ( CH 3 ) 2 CHBr
(A)
It is not always easy to predict the position of AlCl3 ,15 25 C
attack on multiply substituted benzene. If the
benzene ring bears different group ortho/ para CH3 CH3
directing group at the 1 and 4 positions, the
position of further substitution is not immedi-
ately clear.
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Page # 34 AROMATIC COMPOUNDSE
(B)
CH3 CH3
CH3
CH3 – C – Cl
AlCl3,CS 25°C
H3C CH3 H3C CH3
(C)
NH2 NH2
Br Br
OH Br H 2O
2
40 , 50 C
Br OH
OH
OH Br Br
Br2
(D)
CS 2 , 0 C
Br
(A) benzoylation
Ph – C –
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16. Statement -1 Phenol is more reactive than (A) I>II>III>IV (B) IV>III>II>I
benzene towards electrophilic substitution re- (C) II>I>III>IV (D) II>III>I>IV
action.
Statement -2 In the case of phenol the inter-
mediate carboation is more resonance stabi-
lized. 20. F NO2 (
CH 3 ) 2 NH
A
DMF
(A) Statement -1 is true Statement -2 is true
and Statement -2 is correct explanation for (i) NaNO 2 HCl 0 5 C
Statement -1
B [JEE 2003]
(ii) H 2 Catalytic Re duction
(B) Statement -1 is true Statement -2 is true
and Statement -2 is not correct explanation
for Statement -1 (A) O2N NH2
(C) Statement -1 is true Statement -2 is false
(D) Statement -1 is false Statement -2 is true
[JEE 2000] H3C
(B) N NH 2
17. Amongst the following the strongest base is H3 C
[JEE 2000]
(A) C6H5NH2 (B) p-O2NC6H4NH2 H 2C
(C) m-O2NC6H4NH2 (D) C6H5CH2NH2
N NO2
18. Statement -1 : In strongly acidic solutions, H 2C
aniline becomes more reactive towards elec- (C)
trophilic reagents [JEE 1982]
NH2
Statement -1 : The amino group being com-
pletely protonated in strongly acidic solution,
H 3C
the lone pair of electrons of the nitrogen is no
longer available for resonance. (D) N NO2
(A) Statement -1 is true Statement -2 is true H 3C
and Statement -2 is correct explanation for
Statement -1
(B) Statement -1 is true Statement -2 is true
and Statement -2 is not the correct explana- NH
tion for Statement -1 Me Me
(C) Statement -1 is true Statement -2 is false
(D) Statement -1 is false Statement -2 is true 21.
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AROMATIC COMPOUNDS Page # 37
NH
23. + Cl – CH 2CH 2 – CH 3 AlCl
3 P
Me Me
(A) ( i)O2 /
Q + Phenol P and Q are respec-
( ii ) H 3O
tively [JEE 2006]
Br
(A) + CH3CH2CHO
NH
Me Me
(B) + CH3COCH3
(B)
Br
(C) + CH3COCH3
NH
Me Me
(C)
Br (D) + CH3CH2CHO
NH
Comprehension Type : (Q.24 to Q.26)
Me Me Reimer -Tiemann reaction introduces an alde-
hyde group on to the aromatic ring of phenol,
ortho to the hydroxyl group. This reaction in-
(D)
volves electrophilic aromatic substitution. This
is a general method for the synthesis of sub-
Br stituted salicyladehydes as depicted below.
[JEE 2007]
OH
22. Which of the following is obtained when 4-
Methylbenzenesulphonic acid is hydrolysed with
excess of sodium acetate ? [JEE 2005]
–+
(A) CH3 COONa I
CH3
(B) CH3 + SO3
ONa OH
–+ CHO CHO
(C) CH3 SO3Na + CH3COOH
aq.HCl
(D) CH3 SO2O.COCH3 + NaOH
CH3 CH3
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Page # 38 AROMATIC COMPOUNDSE
NO2
ONa ONa
CH2Cl CHCl2
(A) (B) N
(D) O2N
H
CH3 CH3
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AROMATIC COMPOUNDS Page # 39
COOH
NO2
(P)
HO COOH
OCH3
(Q) (C) HO
H3C
NO2
OCH3
C
(S)
H3C NO2
COOH OCH3
(A) HO H3C
COOH
NO2 NO2
(D) HO
NO2
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Page # 40 AROMATIC COMPOUNDSE
NHCH3
OH
(B)
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